Herbicidal compositions

ABSTRACT

Herbicides containing compositions of glycolic acid amides and other active ingredients.

This application is a division of application Ser. No. 627,965, filedNov. 3, 1975, now U.S. Pat. No. 4,057,414, issued Nov. 8, 1977.

The present invention application relates to herbicides containingcompositions of sulfonylglycolic acid amides or sulfonylglycolic acidimides.

It is known that pyridazones (German Pat. No. 1,105,232), benzofuranylsulfonates (German Laid-Open Application DOS No. 1,926,139),benzofuranylalkylamino sulfonates (German Laid-Open Application DOS No.2,324,592), azetidine carbothiolates (German Laid-Open Application DOSNo. 2,312,045), fatty acids (German No. 959,066), thiol carbamates (U.S.Pat. No. 3,185,720; U.S. Pat. No. 3,330,821), carbamates (GermanLaid-Open Application DOS No. 1,567,151; German Printed Application DASNo. 1,137,255), pyrazolium compounds (German Laid-Open Application DOSNo. 2,260,485), α-cyanoacrylates (German Laid-Open Application DOS No.1,642,231), anilides (British No. 903,766) and 1,2,4-triazinones (GermanLaid-Open Application DOS No. 2,138,031) have a herbicidal action.However, this action is not always satisfactory.

We have now found that compositions of one or more of these activeingredients and sulfonylglycolic acid amides (German Laid-OpenApplications DOS No. 2,201,432 and 2,334,715) or sulfonylglycolic acidimides (German Laid-Open Application DOS No. 2,219,923), which are knownas individual herbicidal active ingredients, have an unforeseeablysuperior herbicidal action over their individual components.

These compositions consist of

A. A GLYCOLIC ACID AMIDE OF THE FORMULA ##STR1## where X denotes##STR2## R¹ denoting alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl orhaloalkynyl of a maximum of 6 carbon atoms, alkoxyalkyl,haloalkoxyalkyl, alkenoxyalkyl, alkynoxyalkyl or cycloalkyl, and R²denoting phenyl which may bear one or more identical or differentsubstituents, the number of substituents, which may be halogen, loweralkyl of a maximum of 4 carbon atoms, haloalkyl, alkoxy, alkylsulfonyl,alkylaminosulfonyl, cyano, hydroxy, nitro or amino, being from 0 to 3,and the carbonamide nitrogen being a ring member of an optionallybicyclic cycloalkylimine which may be substituted by halogen or loweralkyl; which may contain further hetero atoms in the ring, and which hasa maximum of 9 carbon atoms, and Y denotes ##STR3## R³, R⁴, R⁵ and R⁶denoting alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynylof a maximum of 8 carbon atoms, unsubstituted or substituted phenyl orcycloalkyl of a maximum of 8 carbon atoms, and R⁴ and R⁵ additionallydenoting hydrogen, and

b. a pyridazone derivative of the formula ##STR4## where X denoteschloro, bromo, iodo or methoxy, R¹ denotes phenyl which may besubstituted by methyl, trifluoromethyl or halogen and R² denotes amino,α-hydroxy-β,β,β-trichloroethylamino, acetylamino, haloacetylamino,methoxy, ##STR5## R³ denoting hydrogen, a cation, a unsubstitutedaliphatic amine, unsubstituted or halogen-substituted alkyl or alkenyl,unsubstituted or substituted phenyl or hydroxyethyl, R⁴ denotinghydrogen, methyl, methoxy or ethyl, R⁵ denoting methyl, ethyl ormethoxy, and R⁶ denoting hydrogen or methyl, and ##STR6## where R¹denotes lower alkyl or the group ##STR7## and R² denotes lower alkyl orhas the same meanings as R³ and R⁴ when R¹ is ##STR8## R³ and R⁴denoting hydrogen or an unsubstituted or halogen- or alkoxy-substitutedaliphatic radical of a maximum of 4 carbon atoms, or

d. a benzofuranylalkylamino sulfonate of the formula ##STR9## where R¹denotes hydrogen, lower alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, alkoxy, or radicals such as ##STR10## R⁴ denotingunsubstituted or halogen.

e. a thiol carbamate of the formula ##STR11## where R¹ denotes loweralkyl or an unsubstituted or methyl-substituted cycloaliphatic,bicycloaliphatic or tricycloaliphatic radical, R² denotes lower alkyl,alkenyl or alkynyl, R³ denotes unsubstituted or halogen-substitutedalkyl, alkenyl or benzyl, and X denotes oxygen or sulfur.

Examples of suitable components for compositions according to theinvention are the active ingredients listed below:

    ______________________________________                                         ##STR12##                                                                    R.sup.1         R.sup.2                                                       ______________________________________                                        CH.sub.3        H                                                             CH.sub.3        CH.sub.3                                                      CH.sub.3        C.sub.2 H.sub.5                                               CH.sub.3        CH.sub.2 CH.sub.2 Cl                                          CH.sub.3        n-C.sub.3 H.sub.7                                             CH.sub.3        i-C.sub.3 H.sub.7                                             CH.sub.3        n-C.sub.4 H.sub.9                                             CH.sub.3        sec-C.sub.4 H.sub.9                                           CH.sub.3        i-C.sub.4 H.sub.9                                             CH.sub.3                                                                                       ##STR13##                                                    CH.sub.3                                                                                       ##STR14##                                                    CH.sub.3                                                                                       ##STR15##                                                    C.sub.2 H.sub.5 CH.sub.3                                                      C.sub.2 H.sub.5 C.sub.2 H.sub.5                                               C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 Cl                                          C.sub.2 H.sub.5 n-C.sub.3 H.sub.7                                             C.sub.2 H.sub.5 i-C.sub.3 H.sub.7                                             n-C.sub.3 H.sub.7                                                                             CH.sub.3                                                      n-C.sub.3 H.sub.7                                                                             i-C.sub.3 H.sub.7                                             C.sub.2 H.sub.5 H                                                             i-C.sub.3 H.sub.7                                                                             H                                                             i-C.sub.3 H.sub.7                                                                             CH.sub.3                                                      i-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                               i-C.sub.3 H.sub.7                                                                             CH.sub.2 CH.sub.2 Cl                                          i-C.sub.3 H.sub.7                                                                             n-C.sub.3 H.sub.7                                             i-C.sub.3 H.sub.7                                                                             i-C.sub.3 H.sub.7                                             i-C.sub.3 H.sub.7                                                                             n-C.sub.4 H.sub.9                                             i-C.sub.3 H.sub.7                                                                             sec-C.sub.4 H.sub.9                                           i-C.sub.3 H.sub.7                                                                              ##STR16##                                                    CH.sub.2CHCH.sub.2                                                                            CH.sub.3                                                      CH.sub.2C CH    CH.sub.3                                                      CH.sub.2CCH     i-C.sub.3 H.sub.7                                             n-C.sub.4 H.sub.9                                                                             CH.sub.3                                                      n-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                               n-C.sub.4 H.sub.9                                                                             n-C.sub.3 H.sub.7                                             n-C.sub.4 H.sub.9                                                                             i-C.sub.3 H.sub.7                                             sec.-C.sub.4 H.sub.9                                                                          H                                                             sec-C.sub.4 H.sub.9                                                                           CH.sub.3                                                      sec.-C.sub.4 H.sub.9                                                                          C.sub.2 H.sub.5                                               sec.-C.sub.4 H.sub.9                                                                          CH.sub.2 CH.sub.2 Cl                                          sec.-C.sub.4 H.sub.9                                                                          n-C.sub.3 H.sub.7                                             sec.-C.sub.4 H.sub.9                                                                          i-C.sub.3 H.sub.7                                             i-C.sub.4 H.sub.9                                                                             i-C.sub.3 H.sub.7                                             tert.-C.sub.4 H.sub.9                                                                         CH.sub.3                                                      tert-C.sub.4 H.sub.9                                                                          C.sub.2 H.sub.5                                               tert-C.sub.4 H.sub. 9                                                                         CH.sub.2 CH.sub.2 Cl                                          tert-C.sub.4 H.sub.9                                                                          i-C.sub.3 H.sub.7                                              ##STR17##      H                                                              ##STR18##      CH.sub.3                                                       ##STR19##      C.sub.2 H.sub.5                                                ##STR20##      CH.sub.2 CH.sub.2 Cl                                           ##STR21##      n-C.sub.3 H.sub.7                                              ##STR22##      i-C.sub.3 H.sub.7                                              ##STR23##      n-C.sub.4 H.sub.9                                              ##STR24##      i-C.sub.3 H.sub.7                                             ______________________________________                                         ##STR25##                                                                     R.sup.1         R.sup.2      R.sup.3                                         ______________________________________                                         ##STR26##       CH.sub.3     CH.sub.3                                         ##STR27##       CH.sub.3     CH.sub.3                                         ##STR28##       CH.sub.3     CH.sub.3                                         ##STR29##       CH.sub.3     CH.sub.3                                         ##STR30##       CH.sub.3     C.sub.2 H.sub.5                                  ##STR31##       CH.sub.3     C.sub.2 H.sub.5                                  ##STR32##       CH.sub.3     C.sub.2 H.sub.5                                  ##STR33##       CH.sub.3     C.sub.2 H.sub.5                                  ##STR34##       CH.sub.3     i-C.sub.3 H.sub.7                                ##STR35##       CH.sub.3     i-C.sub.3 H.sub.7                                ##STR36##       CH.sub.3     i-C.sub.3 H.sub.7                                ##STR37##       CH.sub.3     i-C.sub.3 H.sub.7                                ##STR38##       CH.sub.3     i-C.sub.3 H.sub.7                                ##STR39##       C.sub.2 H.sub.5                                                                            CH.sub.3                                         ##STR40##       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                  ##STR41##       C.sub.2 H.sub.5                                                                            n-C.sub.3 H.sub.7                                ##STR42##       C.sub.2 H.sub.5                                                                            i-C.sub.3 H.sub.7                                ##STR43##       C.sub.2 H.sub.5                                                                            i-C.sub.3 H.sub.7                                ##STR44##       i-C.sub.3 H.sub.7                                                                          CH.sub.3                                         ##STR45##       i-C.sub.3 H.sub.7                                                                          CH.sub.3                                         ##STR46##       i-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                  ##STR47##       i-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                ##STR48##       i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                ##STR49##       i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                ##STR50##                                                                                      ##STR51##   i-C.sub.3 H.sub.7                               ______________________________________                                         ##STR52##                                                                    R.sup.3      R.sup.1      R.sup.2                                             ______________________________________                                        CH.sub.3     CH.sub.3     CH.sub.3                                            CH.sub.3     CH.sub.3     C.sub.2 H.sub.5                                     C.sub.2 H.sub.5                                                                            CH.sub.3     CH.sub.3                                            C.sub.2 H.sub.5                                                                            CH.sub.3     C.sub.2 H.sub.5                                     i-C.sub.3 H.sub.7                                                                          CH.sub.3     CH.sub.3                                            i-C.sub.3 H.sub.7                                                                          CH.sub.3     C.sub.2 H.sub.5                                     i-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                     i-C.sub.3 H.sub.7                                                                          CH.sub.3     CH.sub.2 CH.sub.2 Cl                                sec-C.sub.4 H.sub.9                                                                        CH.sub.3     CH.sub.3                                            ______________________________________                                         ##STR53##                                                                    R.sup.1          R.sup.2                                                      ______________________________________                                         ##STR54##       CH.sub.3                                                     i-C.sub.3 H.sub.7                                                                              C.sub.2 H.sub.5                                              i-C.sub.3 H.sub.7                                                                              n-C.sub.3 H.sub.7                                            i-C.sub.3 H.sub.7                                                                              i-C.sub.3 H.sub.7                                            i-C.sub.3 H.sub.7                                                                              n-C.sub.4 H.sub.9                                            tert-C.sub.4 H.sub.9                                                                           CH.sub.3                                                     sec-C.sub.4 H.sub.9                                                                            CH.sub.3                                                     i-C.sub.4 H.sub.9                                                                              CH.sub.3                                                      ##STR55##       CH.sub.3                                                      ##STR56##       CH.sub.3                                                      ##STR57##       C.sub.2 H.sub.5                                               ##STR58##       n-C.sub.3 H.sub.7                                             ##STR59##       i-C.sub.3 H.sub.7                                             ##STR60##       n-C.sub.4 H.sub.9                                             ##STR61##                                                                                      ##STR62##                                                    ##STR63##                                                                                      ##STR64##                                                   i-C.sub.3 H.sub.7                                                                              CH.sub.3                                                      ##STR65##       CH.sub.3                                                     ______________________________________                                         ##STR66##                                                                    R.sup.1  R.sup.2            R.sup.3                                           ______________________________________                                         ##STR67##                                                                             CH.sub.2 OCH.sub.3 CH.sub.3                                           ##STR68##                                                                             CH.sub.2OCH.sub.3  CH.sub.3                                           ##STR69##                                                                             CH.sub.2OCH.sub.3  CH.sub.3                                           ##STR70##                                                                             CH.sub.2OCH.sub.3  CH.sub.2 Cl                                        ##STR71##                                                                             CH.sub.2OCH.sub.3  C.sub.2 H.sub.5                                    ##STR72##                                                                             CH.sub.2OCH.sub.3  i-C.sub.3 H.sub.7                                  ##STR73##                                                                             CH.sub.2OCH.sub.3  CH.sub.3                                           ##STR74##                                                                             CH.sub.2OCH.sub.3  C.sub.2 H.sub.5                                    ##STR75##                                                                             CH.sub.2OC.sub.2 H.sub.5                                                                         CH.sub.3                                           ##STR76##                                                                             CH.sub.2OC.sub.2 H.sub.5                                                                         CH.sub.3                                           ##STR77##                                                                             CH.sub.2OC.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                    ##STR78##                                                                             CH.sub.2OC.sub.2 H.sub.5                                                                         i-C.sub.3 H.sub.7                                  ##STR79##                                                                             CH.sub.2OC.sub.2 H.sub.5                                                                         CH.sub.3                                           ##STR80##                                                                             CH.sub.2 OC.sub.2 H.sub.5                                                                        CH.sub.2CH(CH.sub.3).sub.2                         ##STR81##                                                                             CH.sub.2OC.sub.3 H.sub.7 n                                                                       CH.sub.3                                           ##STR82##                                                                             CH.sub.2OC.sub.3 H.sub.7 n                                                                       C.sub.2 H.sub.5                                    ##STR83##                                                                             CH.sub.2OCH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                    ##STR84##                                                                              ##STR85##         C.sub.2 H.sub.5                                    ##STR86##                                                                             CH.sub.2OCH(CH.sub.3).sub.2                                                                      CH.sub.3                                           ##STR87##                                                                              ##STR88##         CH.sub.3                                           ##STR89##                                                                             CH.sub.2OC.sub.3 H.sub.7 n                                                                       CH.sub.3                                           ##STR90##                                                                             CH.sub.2OCH(CH.sub.3).sub.2                                                                      CH.sub.3                                           ##STR91##                                                                             CH.sub.2OC.sub.3 H.sub.7 n                                                                       CH.sub.3                                           ##STR92##                                                                             CH.sub.2OCH.sub.2CHCH.sub.2                                                                      CH.sub.3                                           ##STR93##                                                                             CH.sub.2OCH.sub.2CCH                                                                             CH.sub.3                                           ##STR94##                                                                             CH.sub.2OCH(CH.sub.3).sub.2                                                                      CH.sub.3                                           ##STR95##                                                                             CH.sub.2OCH(CH.sub.3)C.sub.2 H.sub.5                                                             CH.sub.3                                           ##STR96##                                                                             CH.sub.2OC(CH.sub.3).sub.3                                                                       CH.sub.3                                           ##STR97##                                                                             CH.sub.2OCH(CH.sub.3)C.sub.2 H.sub.5                                                             C.sub.2 H.sub.5                                    ##STR98##                                                                             CH.sub.2OCH.sub.2CHCH.sub.2                                                                      CH.sub.3                                           ##STR99##                                                                             CH.sub.2OCH.sub.2CH(CH.sub.3).sub.2                                                              CH.sub.3                                          ______________________________________                                         ##STR100##                                                                   R                n                                                            ______________________________________                                        CH.sub.3         4                                                            C.sub.2 H.sub.5  4                                                            CH.sub.2 CH.sub.2 Cl                                                                           4                                                            i-C.sub.3 H.sub.7                                                                              4                                                            n-C.sub.3 H.sub.7                                                                              4                                                            n-C.sub.4 H.sub.9                                                                              4                                                            sec.-C.sub.4 H.sub.9                                                                           4                                                            i-C.sub.4 H.sub.9                                                                              4                                                            CH.sub.3         5                                                            C.sub.2 H.sub.5  5                                                            n-C.sub.3 H.sub.7                                                                              5                                                            i-C.sub.3 H.sub.7                                                                              5                                                            n-C.sub.4 H.sub.9                                                                              5                                                            CH.sub.3         6                                                            C.sub.2 H.sub.5  6                                                            CH.sub.2 CH.sub.2 Cl                                                                           6                                                            n-C.sub.3 H.sub.7                                                                              6                                                            i-C.sub.3 H.sub.7                                                                              6                                                            n-C.sub.4 H.sub.9                                                                              6                                                            sec.-C.sub.4 H.sub.9                                                                           6                                                            CH(C.sub.2 H.sub.5).sub.2                                                                      6                                                            CH.sub.2CH(CH.sub.3)C.sub.2 H.sub.5                                                            6                                                            CH.sub.3         7                                                            C.sub.2 H.sub.5  7                                                            i-C.sub.3 H.sub.7                                                                              7                                                            n-C.sub.3 H.sub.7                                                                              7                                                            CH.sub.2CH.sub.2Cl                                                                             7                                                            H                8 (bicyclo)                                                  CH.sub.3         8 (bicyclo)                                                  C.sub.2 H.sub.5  8 (bicyclo)                                                  i-C.sub.3 H.sub.7                                                                              8 (bicyclo)                                                  n-C.sub.3 H.sub.7                                                                              8 (bicyclo)                                                  n-C.sub.4 H.sub.9                                                                              8 (bicyclo)                                                  sec.-C.sub.4 H.sub.9                                                                           8 (bicyclo)                                                  i-C.sub.4 H.sub.9                                                                              8 (bicyclo)                                                  ______________________________________                                         ##STR101##                                                                   R.sup.1          R.sup.2                                                      ______________________________________                                         ##STR102##      CH.sub.3                                                     "                C.sub.2 H.sub.5                                              "                n-C.sub.3 H.sub.7                                            "                i-C.sub.3 H.sub.7                                            "                n-C.sub.4 H.sub.9                                            "                CH.sub.2CHCH.sub.2                                            ##STR103##      i-C.sub.3 H.sub.7                                            "                C.sub.2 H.sub.5                                               ##STR104##      CH.sub.3                                                     "                C.sub.2 H.sub.5                                              "                i-C.sub.3 H.sub.7                                             ##STR105##      C.sub.2 H.sub.5                                              "                i-C.sub.3 H.sub.7                                             ##STR106##      CH.sub.3                                                     "                C.sub.2 H.sub.5                                              "                n-C.sub.3 H.sub.7                                            "                i-C.sub.3 H.sub.7                                            ______________________________________                                         ##STR107##                                                                   R.sup.1  R.sup.2                 X                                            ______________________________________                                         ##STR108##                                                                            NH.sub.2                Cl                                           "        NH.sub.2                Br                                           "        NHCHOHCCl.sub.3         Br                                                     ##STR109##             Cl                                           "                                                                                       ##STR110##             Br                                           "                                                                                       ##STR111##             Br                                           "                                                                                       ##STR112##             Br                                           "                                                                                       ##STR113##             Br                                           "                                                                                       ##STR114##             Br                                           "                                                                                       ##STR115##             Br                                           "                                                                                       ##STR116##             Br                                           "                                                                                       ##STR117##             Br                                           "                                                                                       ##STR118##             Br                                           "                                                                                       ##STR119##             Br                                           "                                                                                       ##STR120##             Br                                           "                                                                                       ##STR121##             Br                                           "        OCH.sub.3               Cl                                           "        OCH.sub.3               Br                                           "        OCH.sub.3               OCH.sub.3                                    "                                                                                       ##STR122##             Br                                           "                                                                                       ##STR123##             Br                                           "                                                                                       ##STR124##             Br                                            ##STR125##                                                                            NH.sub.2                Cl                                           "        NH.sub.2                Br                                           "                                                                                       ##STR126##             Br                                           "        OCH.sub.3               Br                                           "        OCH.sub.3               Cl                                           "        OCH.sub.3               OCH.sub.3                                    "                                                                                       ##STR127##             Br                                            ##STR128##                                                                            NH.sub.2                Cl                                           "        NH.sub.2                Br                                           "        NHCHOHCCL.sub.3         Br                                           "        NHCHOHCCl.sub.3         Cl                                           "                                                                                       ##STR129##             Cl                                           "                                                                                       ##STR130##             Br                                           "                                                                                       ##STR131##             Cl                                           "        NHC.sub.2 H.sub.5       Cl                                           "                                                                                       ##STR132##             Br                                           "                                                                                       ##STR133##             Br                                           "                                                                                       ##STR134##             Br                                           "                                                                                       ##STR135##             Br                                           "                                                                                       ##STR136##             Cl                                           "                                                                                       ##STR137##             Cl                                           "                                                                                       ##STR138##             Br                                           "        NHCH.sub.3              Cl                                           "        NHCH.sub.3              Br                                           "        OCH.sub.3               Cl                                           "        OCH.sub.3               Br                                           "        OCH.sub.3               OCH.sub.3                                    "        NHOCH.sub.3             Cl                                            ##STR139##                                                                            NH.sub.2                Br                                           "        NHCHOHCCl.sub.3         Cl                                           "        NH.sub.2                Cl                                           "        OCH.sub.3               OCH.sub.3                                    "        OCH.sub.3               Br                                            ##STR140##                                                                            OCH.sub.3               OCH.sub.3                                     ##STR141##                                                                            OCH.sub.3               OCH.sub.3                                     ##STR142##                                                                            OCH.sub.3               OCH.sub.3                                     ##STR143##                                                                            OCH.sub.3               OCH.sub.3                                     ##STR144##                                                                            NH.sub.2                J                                            "        OCH.sub.3               J                                            "                                                                                       ##STR145##             J                                            "                                                                                       ##STR146##             J                                            "                                                                                       ##STR147##             Cl                                           "                                                                                       ##STR148##             Br                                           "                                                                                       ##STR149##             Cl                                           "                                                                                       ##STR150##             Cl                                           "                                                                                       ##STR151##             Br                                           "        NHCHOHCCl.sub.3         Cl                                           "                                                                                       ##STR152##             Cl                                           "        NCHNHCH.sub.3           Br                                           "        NCHNHCH.sub.3           Cl                                           "                                                                                       ##STR153##             Br                                           "        NHCOSC.sub.2 H.sub.5    Cl                                           "                                                                                       ##STR154##             Br                                           "                                                                                       ##STR155##             Cl                                           "                                                                                       ##STR156##             Br                                           "                                                                                       ##STR157##             Br                                           "                                                                                       ##STR158##             Br                                           ______________________________________                                         ##STR159##                                                                   R.sup.1   R.sup.2        R.sup.3                                              ______________________________________                                        i-C.sub.3 H.sub.7                                                                       i-C.sub.3 H.sub.7                                                                            CH.sub.2CClCHCl                                      i-C.sub.3 H.sub.7                                                                       i-C.sub.3 H.sub.7                                                                            CH.sub.2CClCCl.sub.2                                 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                            C.sub.2 H.sub.5                                      i-C.sub.4 H.sub.9                                                                       i-C.sub.4 H.sub.9                                                                            C.sub.2 H.sub.5                                      n-C.sub.4 H.sub.9                                                                       C.sub.2 H.sub.5                                                                              n-C.sub.3 H.sub.7                                    n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                            n-C.sub.3 H.sub.7                                    n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                            tert.-C.sub.4 H.sub.9                                C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                               ##STR160##                                           ##STR161##                                                                             C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                       ##STR162##                                                                             C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                      "         C.sub.2 H.sub.5                                                                              CH.sub.3                                             "         C.sub.2 H.sub.5                                                                              i-C.sub.3 H.sub.7                                     ##STR163##                                                                             C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                       ##STR164##                                                                             C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                       ##STR165##                                                                             CH.sub.2CHCH.sub.2                                                                           C.sub.2 H.sub.5                                                 ##STR166##    C.sub.2 H.sub.5                                      "                                                                                        ##STR167##    C.sub.2 H.sub.5                                       ##STR168##                                                                    ##STR169##                                                                   ______________________________________                                    

sulfurous acid esters of glycolic acid amides, azetidine carbothioatesand butynyl carbamates may also be used as components in addition to theactive ingredients listed above.

The sulfurous acid esters of glycolic acid amides (a) may be obtained byreacting a glycolic acid amide with an alkyl chlorosulfinate at 10° to15° C. in an inert solvent and in the presence of an agent capable ofbinding hydrogen chloride.

For instance, O-ethyl-O-(1-carbonylmethylazacycloheptane)-sulfite may beprepared by dripping a solution of 12.9 parts by weight of ethylchlorosulfinate in 50 parts by weight of benzene at 10° to 15° into 15.7parts by weight of glycolic acid hexamethylene amide dissolved togetherwith 8 parts by weight of pyridine in 50 parts by weight of dry benzene.After 30 minutes the precipitated pyridinium hydrochloride is filteredoff and the organic phase washed with water. After drying has beeneffected, the benzene is distilled off. There is obtained 20.4 parts byweight of the desired product. The compound has the following structure:##STR170## n₂₅ = 1.4910.

The following active ingredients may for example be used:

N-methylacetanilido-(α-ethylsulfite)

N-methylacetanilido-(α-isopropylsulfite)

N-(butyn-1-yl-3)-acetanilido-(α-ethylsulfite)

N-(butyn-1-yl-3)-acetanilido-(α-isopropylsulfite)

N-(butyn-1-yl-3)-acetanilido-(α-methylsulfite) m.p.: 69° to 70° C.

N-isopropylacetanilido-(α-methylsulfite) m.p.: 60° to 61° C.

N-ethylacetanilido-(α-propylsulfite) n₂₅ ^(D) : 1.5295

N-ethylacetanilido-(α-isopropylsulfite) n₂₅ ^(D) : 1.5164

N-ethylacetanilido-(α-methylsulfite) n₂₅ ^(D) : 1.5118

N-ethylacetanilido-(α-ethylsulfite) n₂₅ ^(D) : 1.5010

N-methyl-(4-methoxyacetanilido)-(α-isopropylsulfite)

N-(butyn-1-yl-3)-(4-methoxyacetanilido)-(α-isopropylsulfite)

N-methyl-(p-methylacetanilido)-(α-isopropylsulfite)

N-butyn-1-yl-3)-(p-methylacetanilido)-(α-isopropylsulfite)

N-(2-methylbenzyl)-acetanilido-(α-methylsulfite)

N-(2-methylbenzyl)-acetanilido-(α-ethylsulfite)

N-(2-methylbenzyl)-acetanilido-(α-propylsulfite)

N-(2-methylbenzyl)-acetanilido-(α-isopropylsulfite)

N-tert-butylacetanilido-(α-isopropylsulfite) m.p.: 78° C.

N-tert-butylacetanilido-(α-methylsulfite) m.p.: 57° C.

N-methylacetanilido-(α-sec-butylsulfite), n₂₅ = 1.5083

N-(butyn-1-yl-3)-acetanilido-(α-isobutylsulfite) n₂₅ : 1.5098

N-(butyn-1-yl-3)-acetanilido-(α-sec-butylsulfite) n₂₅ : 1.5132

N-(butyn-1-yl-3)-acetanilido-(α-n-butylsulfite) n₂₅ : 1.5172

N-isobutylacetanilido-(α-methylsulfite) n₂₅ : 1.5229

N-isobutylacetanilido-(α-ethylsulfite) n₂₅ : 1.5100

N-methylacetanilido-(α-n-butylsulfite) n₂₅ : 1.5144

N-isobutylacetanilido-(α-propylsulfite) n₂₅ : 1.5059

N-isobutylacetanilido-(α-isopropylsulfite) n₂₅ : 1.5028

N-methylacetanilido-(α-methylsulfite)

N-methylacetanilido-(α-isobutylsulfite)

N-(buty-1-yl-3)-acetanilido-(α-methylsulfite)

N-methyl-(2-methylacetanilido)-(α-methylsulfite)

N-methyl-(4-methylacetanilido)-(α-methylsulfite)

N-methyl-(4-methoxyacetanilido)-(α-methylsulfite)

N-methyl-(3-chloroacetanilido)-(α-methylsulfite)

N-methyl-(2-methylacetanilido)-(α-ethylsulfite)

N-methylacetanilido-[α-(1-methyl-2-methoxy)-ethylsulfite]

N-methyl-(4-methylacetanilido)-(α-ethylsulfite)

N-methyl-(4-methoxyacetanilido)-(α-ethylsulfite)

N-methyl-(3-chloroacetanilido)-(α-ethylsulfite)

N-methyl-(2-methylacetanilido)-(α-isopropylsulfite)

N-methyl-(3-chloroacetanilido)-(α-isopropylsulfite)

N-methyl-(4-methylacetanilido)-(α-n-butylsulfite)

O-methyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.4955

O-isopropyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.4695

O-butyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.4875

O-propyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.4828

O-isopropyl-O-(1-carbonylmethylazacycloheptane)-sulfite; m.p. = 58° to59° C.

O-ethyl-O-(1-carbonylmethyl-2-methylazacycloheptane)-sulfite; n₂₅ =1.4882

O-isopropyl-O-(1-carbonylmethyl-2-methylazacycloheptane)-sulfite; n₂₅ =1.4740

O-methyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ =1.4952

O-ethyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ =1.4860

O-propyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ =1.4849

O-isopropyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite;n₂₅ = 1.4749

O-ethyl-O-(1-carbonylmethyl-3,5,5-trimethyl-(3,3,5-trimethyl)-azacycloheptane)-sulfite;n₂₅ = 1.4850

(1:1 isomer mixture of the 3,3,5- and 3,5,5-trimethyl derivative)

O-isopropyl-O-(1-carbonylmethyl-3-methyl-(2-methyl)-azacycloheptane)-sulfite;n₂₅ = 1.4735 (isomer mixture, 55% of which being the 3-methyl and 45% ofwhich the 2-methyl derivative)

O-ethyl-O-(1-carbonylmethylazacycloheptane)-sulfite

O-n-propyl-O-(1-carbonylmethylazacycloheptane)-sulfite

O-methyl-O-(1-carbonylmethyl-3-methylazacycloheptane)-sulfite

O-ethyl-O-(1-carbonylmethyl-3-methylazacycloheptane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-3-methylazacycloheptane)-sulfite

O-ethyl-O-(1-carbonylmethyl-4-methylazacycloheptane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-4-methylazacycloheptane)-sulfite

O-methyl-(1-carbonylmethyl-3-azabicyclo-[3,2,0]-heptane)-sulfite

O-ethyl-(1-carbonylmethyl-3-azabicyclo-[3,2,0]-heptane)-sulfite

O-n-propyl-(1-carbonylmethyl-3-azabicyclo-[3,2,0]-heptane)-sulfite

O-isopropyl-(1-carbonylmethyl-3-azabicyclo-[3,2,0]-heptane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-2-methyl-(3-methyl)-azacycloheptane)-sulfite;n₂₅ = 1.4698

(isomer mixture, 75% of which is the 2-methyl and 25% of which the3-methyl derivative)

O-allyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite n₂₅ =1.4970

O-allyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.5026

O-(butyn-1-yl-3)-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite;n₂₅ = 1.4929

O-(butyn-1-yl-3)-O-(1-carbonylmethyl-3-methylazacycloheptane)-sulfite;n₂₅ = 1.4965

O-ethyl-O-(1-carbonylmethylazacyclohexane)-sulfite

O-isopropyl-O-(1-carbonylmethylazacyclohexane)-sulfite

O-methyl-O-(1-carbonylmethyl-2-methylazacyclohexane)-sulfite

O-allyl-O-(1-carbonylmethyl-2-methylazacyclohexane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-2-methylazacyclohexane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-3-methylazacyclohexane)-sulfite

O-(β-chloroethyl)-O-(1-carbonylmethyl-3-methylazacyclohexane)-sulfite

O-ethyl-O-(1-carbonylmethyl-4-methylazacyclohexane)-sulfite

O-allyl-O-(1-carbonylmethyl-4-methylazacyclohexane)-sulfite

O-(β-chloroethyl)-O-(1-carbonylmethyl-4-methylazacyclohexane)-sulfite

O-methyl-O-(1-carbonylmethyl-3,3-dimethylazacyclohexane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-3,3-dimethylazacyclohexane)-sulfite

O-(β-chloroethyl)-O-(1-carbonylmethyl-3,5,5-trimethyl)-(3,3,5-trimethylazacycloheptane)-sulfite

(1:1 isomer mixture of the 3,5,5- and the 3,3,5-trimethyl derivative).

A component may make up from 5 to 95 wt%, preferably 20 to 80 wt%, of anactive ingredient composition according to the invention.

The amount used of the agents according to the invention may vary anddepends in essence on the type of effect to be achieved; it is generallyfrom 0.1 to 15 (and more), preferably from 0.2 to 6, kg per hectare ofactive ingredient. The agents according to the invention may be usedonce or several times before of after planting, before sowing, andbefore, during or after emergence of the crop plant and unwanted plants.

Application may be effected for instance in the form of directlysprayable solutions, powders, suspensions, (including high-percentageoily or aqueous suspensions) dispersions, emulsions, oil dispersions,pastes, dusts, broadcasting agents, or granules by spraying, atomizing,dusting, broadcasting or watering. The forms of application dependentirely on the purpose for which the agents are being used; in any casethey should ensure a fine distribution of the active ingredient.

For the preparation of solutions, emulsions, pastes and oil dispersionsto be sprayed direct, mineral oil fractions of medium to high boilingpoint, such as kerosene or diesel oil, further coal-tar oils, etc. andoils of vegetable or animal origin, aliphatic, cyclic and aromatichydrocarbons such as benzene, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes and their derivatives suchas methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,etc., and strongly polar solvents such as dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes,oil dispersions or wettable powders by adding water. To prepareemulsions, pastes and oil dispersions the ingredients as such ordissolved in an oil or solvent may be homogenized in water by means ofwetting or dispersing agents, adherents or emulsifiers. Concentrateswhich are suitable for dilution with water may be prepared from activeingredient, wetting agent, adherent, emulsifying or dispersing agent andpossibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal andammonium salts of ligninsulfonic acid, naphthalenesulfonic acids,phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkylsulfonates, alkali metal and alkaline earth metal salts ofdibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcoholsulfates, alkali metal and alkaline earth metal salts of fatty acids,salts of sulfated hexadecanols, heptadecanols, and octadecanols, saltsof sulfated fatty alcohol glycol ether, condensation products ofsulfonated naphthalene and naphthalene derivatives with formaldehyde,condensation products of naphthalene or naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol,alkylphenol polyglycol ethers, tributylphenol polyglycol ethers,alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcoholethylene oxide condensates, ethoxylated caster oil, polyoxyethylenealkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycolether acetal, sorbitol esters, lignin, sulfite waste liquors and methylcellulose.

Powders, dusts and broadcasting agents may be prepared by mixing orgrinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may beprepared by bonding the active ingredients to solid carriers. Examplesof solid carriers are mineral earths such as silica gel, silicic acid,silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk,bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground plastics, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, andvegetable products such as grain flours, bark meal, wood meal, andnutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90%, byweight of active ingredient.

There may be added to the compositions or individual active ingredients(if desired, immediately before use (tankmix)) oils of various types,wetting agents or adherents, herbicides, fungicides, nematocides,insecticides, bactericides, trace elements, fertilizers antifoams (e.g.,silicones), growth regulators, antidotes and other herbicidallyeffective compounds such as

substituted anilines

substituted aryloxycarboxylic acids and salts, esters and amidesthereof,

substituted ethers

substituted arsonic acids and their salts, esters and amides

substituted benzimidazoles

substituted benzisothiazoles

substituted benzothiadiazinone dioxides

substituted benzoxazines

substituted benzoxazinones

substituted benzothiadiazoles

substituted biurets

substituted quinolines

substituted carbamates

substituted aliphatic carboxylic acids and their salts, esters andamides

substituted aromatic carboxylic acids and their salts, esters and amides

substituted carbamoylalkylthiol- or -dithiophosphates

substituted quinazolines

substituted cycloalkylamidocarbothiolic acids and their salts, estersand amides

substituted cycloalkylcarbonamidothiazoles

substituted dicarboxylic acids and their salts, esters and amides

substituted dihydrobenzofuranyl sulfonates

substituted disulfides

substituted dipyridylium salts

substituted dithiocarbamates

substituted dithiophosphoric acids and their salts, esters and amides

substituted ureas

substituted hexahydro-1H-carbothioates

substituted hydantoins

substituted hydrazides

substituted hydrazonium salts

substituted isoxazole pyrimidones

substituted imidazoles

substituted isothiazole pyrimidones

substituted ketones

substituted naphthoquinones

substituted aliphatic nitriles

substituted aromatic nitriles

substituted oxadiazoles

substituted oxadiazinones

substituted oxadiazolidine diones

substituted oxadiazine diones

substituted phenols and their salts and esters

substituted phosphonic acids and their salts, esters and amides

substituted phosphonium chlorides

substituted phosphonalkyl glycines

substituted phosphites

substituted phosphoric acids and their salts, esters and amides

substitutes piperidines

substituted pyrazoles

substituted pyrazole alkylcarboxylic acids and their salts, esters andamides

substituted pyrazolium salts

substituted pyrazolium alkyl sulfates

substituted pyridazines

substituted pyridazones

substituted pyridine carboxylic acids and their salts, esters and amides

substituted pyridines

substituted pyridine carboxylates

substituted pyridinones

substituted pyrimidines

substituted pyrimidones

substituted pyrrolidine carboxylic acid and its salts, esters and amides

substituted pyrrolidines

substituted pyrrolidones

substituted arylsulfonic acids and their salts, esters and amides

substituted styrenes

substituted tetrahydrooxadiazine diones

substituted tetrahydroxadiazole diones

substituted tetrahydromethanoindenes

substituted tetrahydroxadiazole thiones

substituted tetrahydrothiadiazine thiones

substituted tetrahydrothiadiazole diones

substituted aromatic thiocarbonylamides

substituted thiocarboxylic acids and their salts, esters and amides

substituted thiol carbamates

substituted thioureas

substituted thiophosphoric acids and their salts, esters and amides

substituted triazines

substituted triazoles

substituted uracils, and

substituted uretidine diones.

The last-mentioned herbicidal compounds may also be applied before orafter the compositions according to the invention.

These agents may be added to the compositions according to the inventionin a ratio by weight of from 1:10 to 10:1. The same applies to oils,fungicides, nematocides, insecticides, bactericides, antidotes andgrowth regulators.

The new compositions have a strong herbicidal action and may thereforebe used as weedkillers or for controlling the growth of unwanted plants.Whether the new active ingredients are used as total or selective agentsdepends in essence on the amount of ingredient used per unit area.

By weeds and unwanted plant growth are meant all monocotyledonous anddicotyledonous plants which grow in loci where they are not desired.

The agents according to the invention may therefore be used forcontrolling for instance Gramineae, such as

    ______________________________________                                        Cynodon spp.        Dactylis spp.                                             Digitaria spp.      Avena spp.                                                Echinochloa spp.    Bromus spp.                                               Setaria spp.        Uniola spp.                                               Panicum spp.        Poa spp.                                                  Alopecurus spp.     Leptochloa spp.                                           Lolium spp.         Brachiaria spp.                                           Sorghum spp.        Eleusine spp.                                             Agropyron spp.      Cenchrus spp.                                             Phalaris spp.       Eragrostis spp.                                           Apera spp.          Phragmites communis                                       etc.;                                                                         Cyperaceae, such as                                                           Carex spp.          Eleocharis spp.                                           Cyperus spp.        Scirpus spp.                                              etc.;                                                                         dicotyledonous weeds, such as                                                 Malvaceae, e.g.                                                               Abutilon theoprasti Hibiscus spp.                                             Sida spp.           Malva spp.                                                etc.;                                                                         Compositae, such as                                                           Ambrosia spp.       Centaurea spp.                                            Lactuca spp.        Tussilago spp.                                            Senecio spp.        Lapsana communis                                          Sonchus spp.        Tagetes spp.                                              Xanthium spp.       Erigeron spp.                                             Iva spp.            Anthemis spp.                                             Galinsoga spp.      Matricaria spp.                                           Taraxacum spp.      Artemisia spp.                                            Chrysanthemum spp.  Bidens spp.                                               Cirsium spp.        etc.;                                                     Convolvulaceae, such as                                                       Convolvulus spp.    Cuscuta spp.                                              Ipomoea spp.        Jaquemontia tamnifolia                                    etc.;                                                                         Cruciferae, such as                                                           Barbarea vulgaris   Arabidopsis thaliana                                      Brassica spp.       Descurainia spp.                                          Capsella spp.       Draba spp.                                                Sisymbrium spp.     Coronopus didymus                                         Thlaspi spp.        Lepidium spp.                                             Sinapis arvensis    Raphanus spp.                                             etc.;                                                                         Geraniaceae, such as                                                          Erodium spp.        Geranium spp.                                             etc.;                                                                         Portulacaceae, such as                                                        Portulaca spp.      etc.;                                                     Primalaceae, such as                                                          Anagallis arvensis  Lysimachia spp.                                           etc.;                                                                         Rubiaceae, such as                                                            Richardia spp.      Diodia spp.                                               Galium spp.         etc.;                                                     Scrophulariacea, such as                                                      Linaria spp.        Digitalis spp.                                            Veronica spp.       etc.;                                                     Solanaceae, such as                                                           Physalis spp.       Nicandra spp.                                             Solanum spp.        Datura spp.                                               etc.;                                                                         Urticaceae, such as                                                           Urtica spp.                                                                   Violaceae, such as                                                            Viola spp.          etc.;                                                     Zygophyllaceae, such as                                                       Tribulus terrestris etc.;                                                     Euphorbiaceae, such as                                                        Mercurialis annua   Euphorbia spp.                                            Umbelliferae, such as                                                         Daucus carota       Ammi majus                                                Aethusa cynapium    etc.;                                                     Commelinaceae, such as                                                        Commelina spp.      etc.;                                                     Labiatae, such as                                                             Lamium spp.         Galeopsis spp.                                            etc.;                                                                         Leguminosae, such as                                                           Medicago spp.      Sesbania exaltata                                         Trifolium spp.      Cassia spp.                                               Vicia spp.          Lathyrus spp.                                             etc.;                                                                         Plantaginaceae, such as                                                       Plantago spp.       etc.;                                                     Polygonaceae, such as                                                         Polygonum spp.      Fagopyrum spp.                                            Rumex spp.          etc.;                                                     Aizoaceae, such as                                                            Mollugo verticillata                                                                              etc.;                                                     Amaranthaceae, such as                                                        Amaranthus spp.     etc.;                                                     Boraginaceae, such as                                                         Amsinckia spp.      Anchusa spp.                                              Myostis spp.        Lithospermum spp.                                         etc.;                                                                         Caryophyllaceae, such as                                                      Stellaria spp.      Silene spp.                                               Spergula spp.       Cerastium spp.                                            Saponaria spp.      Agrostemma githago                                        Scleranthus annuus  etc.;                                                     Chenopodiaceae, such as                                                       Chenopodium spp.    Atriplex spp.                                             Kochia spp.         Monolepsis nuttalliana                                    Salsola Kali        etc.;                                                     Lythraceae, such as                                                           Cuphea spp.         etc.;                                                     Oxalidaceae, such as                                                          Oxalis spp.                                                                   Ranunculaceae, such as                                                        Ranunculus spp.     Adonis spp.                                               Delphinium spp.     etc.;                                                     Papaveraceae, such as                                                         Papaver spp.        Fumaria offinicalis                                       etc.;                                                                         Onagraceae, such as                                                           Jussiaea spp.       etc.;                                                     Rosaceae, such as                                                             Alchemillia spp.    Potentilla spp.                                           etc.;                                                                         Potamogetonaceae, such as                                                     Potamogeton spp.    etc.;                                                      Najadaceae, such as                                                          Najas spp.          etc.;                                                     Equisetaceae                                                                  Equisetum spp.      etc.;                                                     Marsileaceae, such as                                                         Marsilea quadrifolia                                                                              etc.;                                                     Polypodiaceae,                                                                Pteridium quilinum                                                            Alismataceae, such as                                                         Alisma spp.         Sagittaria sagittifolia                                   etc.                                                                          The herbicides according to the invention may be employed                     in cereal crops such as                                                       Avena spp.          Sorghum                                                   Triticum spp.       Zea mays                                                  Hordeum spp.        Panicum miliaceum                                         Secale spp.         Oryza spp.                                                Saccharum offinicarum                                                         and in dicotyledon crops such as                                              Cruciferae, e.g.                                                              Brassica spp.       Raphanus spp.                                             Sinapis spp.        Lepidium spp.                                             Compositea e.g.                                                               Lactuca spp.        Carthamus spp.                                            Helianthus spp.     Scorzonera spp.                                           malvaceae, e.g.                                                               Gossypium hirsutum                                                            Leguminosae, e.g.                                                             Medicago spp.       Phaseolus spp.                                            Trifolium spp.      Arachis spp.                                              Pisum spp.          Glycine max.                                              Chenopodiaceae, e.g.                                                          Beta vulgaris                                                                 Spinacia spp.                                                                 Solanaceae, e.g.                                                              Solanum spp.        Capsicum annuum                                           Nicotiania spp.                                                               Linaceae,e.g.                                                                 Linum spp.                                                                    Umbelliferae, e.g.                                                            Petroselinum spp.   Apiam graveolens                                          Daucus carota                                                                 Rosaceae e.g.       Fragaria                                                  Cucurbitaceae, e.g.                                                           Cucumis spp.        Cucurbita spp.                                            Liliaceae e.g.                                                                Allium spp.                                                                   Vitaceae, e.g.                                                                Vitis vinifera                                                                Bromeliaceae, e.g.                                                            Ananas sativus.                                                               ______________________________________                                    

The compositions may also be used as total agents on ditches, aquaticareas, railway track, waste and barren land, etc.

The compositions according to the invention were tested in thegreenhouse and in the open. Their action corresponds to that of thecompositions employed in the following examples.

EXAMPLE 1

An agricultural plot was sown with various seeds. The soil was thenimmediately treated with the following amounts of the followingindividual active ingredients and compositions thereof as dispersions,emulsions or granules:

I 1-phenyl-4-amino-5-chloropyridazone-(6)

Iii o-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide

Iv 2,3-dichloroallyl N,N-diisopropylthiolcarbamate

V 2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate

Vi 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethane sulfonate

Viii 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yldimethylaminosulfonate

Ix ethyl N-ethyl-N-cyclohexylthiocarbamate, each at rates of 0.5, 1 and2 kg/ha;

    I+III+IV, I+III+V, I+III+VI, I+III+VIII and I+III+IX,

each at rates of 1+0.5+0.5, 0.5+1+0.5 and 0.5+0.5+1 kg/ha.

After 4 to 5 weeks it was ascertained that the compositions had a betterherbicidal action than their components, combined with the same croptolerance.

The results are given below:

    __________________________________________________________________________    Active ingredient                                                                        I     III    IV                                                    kg/ha      0.5                                                                             1 2 0.5                                                                             1 2  0.5                                                                             1 2                                                 __________________________________________________________________________    Crop plants:                                                                  Beta vulgaris                                                                            0 0 0 0 0 0  0 0 10                                                Unwanted plants:                                                              Avena fatua                                                                              5 12                                                                              20                                                                              15                                                                              40                                                                              54 20                                                                              50                                                                              95                                                Echinochloa crus -galli                                                                  6 13                                                                              32                                                                              25                                                                              70                                                                              100                                                                              10                                                                              20                                                                              50                                                Matricaria chamomilla                                                                    20                                                                              40                                                                              85                                                                              15                                                                              35                                                                              80 5 10                                                                              19                                                Active ingredient                                                                        V     VI    VIII   IX                                              kg/ha      0.5                                                                             1 2 0.5                                                                             1 2 0.5                                                                             1 2  0.5                                                                             1 2                                           __________________________________________________________________________    Beta vulgaris                                                                            0 0 0 2.5                                                                             4 10                                                                              0 0 0  0 0 0                                           Avena fatua                                                                              25                                                                              50                                                                              95                                                                              16                                                                              40                                                                              80                                                                              45                                                                              80                                                                              100                                                                              10                                                                              30                                                                              60                                          Echinochloa crus-galli                                                                   10                                                                              20                                                                              50                                                                              20                                                                              30                                                                              70                                                                              70                                                                              90                                                                              100                                                                              20                                                                              30                                                                              80                                          Matricaria chamomilla                                                                    9 12                                                                              21                                                                              20                                                                              40                                                                              70                                                                              5 20                                                                              50 5 7 10                                          Active ingredient                                                                        I + III +  IV                                                                          I + III + V                                                                            I + III + VI                                     kg/ha      1+ 0.5+                                                                             0.5+                                                                             1+ 0.5+                                                                             0.5+                                                                             1+ 0.5+                                                                             0.5+                                                  0.5+                                                                             1+ 0.5+                                                                             0.05+                                                                            1+ 0.5+                                                                             0.5+                                                                             1+ 0.5+                                                  0.5                                                                              0.5                                                                              1  0.5                                                                              0.5                                                                              1  0.5                                                                              0.5                                                                              1                                          __________________________________________________________________________    Crop plants:                                                                  Beta vulgaris                                                                            0  0  0  0  0  0  2.5                                                                              2.5                                                                              4                                          Unwanted plants:                                                              Avena fatua                                                                              85 95 100                                                                              90 100                                                                              100                                                                              85 90 95                                         Echinochloa crus-galli                                                                   91 100                                                                              100                                                                              98 100                                                                              100                                                                              100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    90 97 85 95 95 90 100                                                                              100                                                                              100                                        Active ingredient                                                                        I + III + VIII                                                                         I + III + IX                                              __________________________________________________________________________    Beta vulgaris                                                                            0  0  0  0  0  0                                                   Avena fatua                                                                              100                                                                              100                                                                              100                                                                              80 90 85                                                  Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              96 100                                                                              100                                                 Matricaria chamomilla                                                                    90 90 95 100                                                                              97 90                                                  __________________________________________________________________________     0 = no damage                                                                 100 = complete destruction                                               

EXAMPLE 2

An agricultural plot was sown with various seeds. The soil was thenimmediately treated with the following amounts of the followingindividual active ingredients and compositions thereof as dispersions oremulsions:

I 1-phenyl-4-amino-5-chloropyridazone-(6)

Iii o-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide

Iv 2,3-dichloroallyl N,N-diisopropylthiolcarbamate

V 2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate

Vi 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethane sulfonate

Viii 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yldimethylaminosulfonate

Ix ethyl N-ethyl-N-cyclohexylthiolcarbamate, each at rates of 1, 1.5, 2,3, 4, 4.5, 5 and 6 kg/ha;

    I+III+IV, I  V, I+III+VI, I+III+VIII and I+III+IX,

each at rates of 1+1+1, 2+1+1, 1+2+1, 1+1+2, 1.5+1.5+1.5, 3+1+1, 1+3+1,1+1+3 and 2+2+2 kg/ha; and for comparison

X n-(4-chlorophenyl)-N',N'-dimethylurea, 3 and 5 kg/ha; I+II+X 1+1+3kg/ha.

After 4 to 5 weeks it was ascertained that the compositions I+III+IV,I+III+V, I+III+VI, I+III+VIII and I+III+IX had better crop tolerencethan the composition I+II+X, combined with the same weed control.

The results are given below:

    __________________________________________________________________________    Active ingredient                                                                        I                                                                  kg/ha      1  1.5                                                                              2   3   4   4.5                                                                              5  6                                          __________________________________________________________________________    Crop plants:                                                                  Beta vulgaris                                                                            0  0  0   0   10  13 15 20                                         Unwanted plants:                                                              Avena fatua                                                                              12 15 20  40  75  85 90 100                                        Echinochloa crus-galli                                                                   13 20 32  65  75  80 90 100                                        Matricaria chamomilla                                                                    40 60 85  100 100 100                                                                              100                                                                              100                                        Active ingredient                                                                        III                                                                __________________________________________________________________________    Beta vulgaris                                                                            0  0  0   0   10   15                                                                              20 30                                         Avena fatua                                                                              40 45 54  75  80   65                                                                              90 85                                         Echinochloa crus-galli                                                                   70 90 100 100 100  100                                                                             100                                                                              100                                        Matricaria chamomilla                                                                    35 65 80  90  95   100                                                                             100                                                                              100                                        Active ingredient                                                                        IV                                                                 kg/ha      1  1.5                                                                              2   3   4   4.5                                                                              5  6                                          __________________________________________________________________________    Beta vulgaris                                                                            0  0  10  15  25  30 35 45                                         Avena fatua                                                                              50 83 95  100 100 100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   20 40 50  80  90  100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    10 13 19  30  40  45 55 70                                         Active ingredient                                                                        V                                                                  __________________________________________________________________________    Beta vulgaris                                                                            0  0  7   10  20  28 35 40                                         Avena fatua                                                                              50 90 95  100 100 100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   20 50 50  90  96  100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    12 15 21  32  45  50 60 75                                         Active ingredient                                                                        VI                                                                 __________________________________________________________________________    Beta vulgaris                                                                            4  5  10  20  25  30 35 40                                         Avena fatua                                                                              40 60 80  100 100 100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   30 70 70  100 100 100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    40 50 70  80  95  100                                                                              100                                                                              100                                        Active ingredient                                                                        VIII                                                               __________________________________________________________________________    Beta vulgaris                                                                            0  0  0   5   10  12 18 25                                         Avena fatua                                                                              80 100                                                                              100 100 100 100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   90 100                                                                              100 100 100 100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    20 30 50  70  92  100                                                                              100                                                                              100                                        Active ingredient                                                                        IX                                                                 __________________________________________________________________________    Beta vulgaris                                                                            0  0  0   0   10  12 15 20                                         Avena fatua                                                                              30 40 60  95  100 100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   30 60 80  95  100 100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    7  9  10  16  48  55 60 75                                                    I + III + IV                                                                  1+ 2+ 1+ 1+ 1.5+                                                                             3+ 1+ 1+ 2+                                         Active ingredient                                                                        1+ 1+ 2+ 1+ 1.5+                                                                             1+ 3+ 1+ 2+                                         kg/ha      1  1  1  2  1.5                                                                              1  1  3  2                                          __________________________________________________________________________    Beta vulgaris                                                                             0  0  0 10  0  0  0  15                                                                               10                                        Avena fatua                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Active ingredient                                                                        I + III + V                                                        __________________________________________________________________________    Beta vulgaris                                                                             0  0  0  7  0  0  0  10                                                                               7                                         Avena fatua                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Active ingredient                                                                        I + III + VI                                                       __________________________________________________________________________    Beta vulgaris                                                                             4  4  4  10                                                                               5  4  4  20                                                                               10                                        Avena fatua                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Active ingredient                                                                        I + III + VIII                                                     __________________________________________________________________________    Beta vulgaris                                                                             0  0  0  0  0  0  0  5  0                                         Avena fatua                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Active ingredient                                                                        I + III + IX                                                       __________________________________________________________________________    Beta vulgaris                                                                             0  0  0  0  0  0  0  0  0                                         Avena fatua                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Matricaria chamomilla                                                                    100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Active ingredient                                                                            X             I+II+X                                           kg/ha          3      5      1+1+3                                            __________________________________________________________________________    Beta vulgaris  100    100    100                                              Avena fatua    100    100    100                                              Echinochloa crus-galli                                                                       100    100    100                                              Matricaria chamomilla                                                                        100    100    100                                              __________________________________________________________________________     0 = no damage                                                                 100 = complete destruction                                               

EXAMPLE 3

In the greenhouse, loamy sandy soil was filled into pots and sown withvarious seeds. The soil prepared in this manner was then treated withthe following amounts of the following individual active ingredients andcompositions thereof as granules:

I 1-phenyl-4-amino-5-chloropyridazone-(6)

Ii o-(isopropylaminosulfonyl)-glycolic acid-N-butyn-1-yl-3-anilide

Iii o-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide,

Xxxxii ethyl N,N-di-n-propylthiolcarbamate

Xxxxiii n-propyl N-ethyl-N-butylthiolcarbamate each at rates of 0.5, 1,1.5 and 2 kg/ha;

    I+II+XXXII, I+II+XXXXIII, I+III+XXXXII and I+III+XXXXIII,

each at rates of 0.5+0.5+0.5, 1+0.5+0.5, 0.5+1+0.5 and 0.5+0.5+1 kg/ha;

    II+XXXXII, II+XXXXIII, III+XXXXII and III+XXXXIII,

each at rates of 0.5+0.5, 1+0.5, 0.5+1 and 1+1 kg/ha.

After 4 to 5 weeks it was ascertained that, at the low applicationrates, the compositions had a better weed control than their components,combined with the same crop tolerance. At the higher application rates,the crop tolerance was still good.

The results are given below:

    __________________________________________________________________________    Active ingredient                                                                        I        II             III                                        kg/ha      0.5                                                                              1  1.5                                                                              2  0.5                                                                              1  1.5                                                                              2  0.5                                                                              1  1.5                                                                              2                                 __________________________________________________________________________    Crop plants:                                                                  Beta vulgaris                                                                            0  0  0  0  0  0  0  0  0  0  0  0                                 Unwanted plants:                                                              Avena fatua                                                                              5  12 15 20 40 60 65 75 15 40 45 54                                Echinochloa crus-galli                                                                   6  13 20 32 60 70 95 100                                                                              60 70 90 100                               Matricaria chamomilla                                                                    20 40 60 85 15 40 60 80 15 35 55 80                                Active ingredient                                                                        XXXXII   XXXXIII                                                   __________________________________________________________________________    Beta vulgaris                                                                            0  0  0  0  0  0  0  0                                             Avena fatua                                                                              20 27 40 54 20 30 45 59                                            Echinochloa crus-galli                                                                   28 45 60 80 24 41 55 75                                            Matricaria chamomilla                                                                    10 26 40 50 20 20 25 35                                                       I + II + XXXXII                                                                           I + II + XXXXIII                                                                          I + III + XXXXII                                      0.5+                                                                             1+ 0.5+                                                                             0.5+                                                                             0.5+                                                                             1+ 0.5+                                                                             0.5+                                                                             0.5+                                                                             1+ 0.5+                                                                             0.5+                              Active ingredient                                                                        0.5+                                                                             0.5+                                                                             1+ 0.5+                                                                             0.5+                                                                             0.5+                                                                             1+ 0.5+                                                                             0.5+                                                                             0.5+                                                                             1+ 0.5+                              kg/ha      0.5                                                                              0.5                                                                              0.5                                                                              1  0.5                                                                              0.5                                                                              0.5                                                                              1  0.5                                                                              0.5                                                                              0.5                                                                              1                                 __________________________________________________________________________    Beta vulgaris                                                                            0  0  0  0  0  0  0  0  0  0  0  0                                 Avena fatua                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              80 89 100                                                                              87                                Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                               Matricaria chamomilla                                                                    85 100                                                                              100                                                                              100                                                                              95 100                                                                              100                                                                              100                                                                              86 100                                                                              100                                                                              100                               Active ingredient                                                                        I + III + XXXXIII                                                  __________________________________________________________________________    Beta vulgaris                                                                            0  0  0  0                                                         Avena fatua                                                                              80 88 100                                                                              92                                                        Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                       Matricaria chamomilla                                                                    95 100                                                                              100                                                                              95                                                                   II + XXXXII II + XXXXIII                                           Active ingredient                                                                        0.5+                                                                             1+ 0.5+                                                                                0.5+                                                                             1+ 0.5+                                             kg/ha      0.5                                                                              0.5                                                                              1  1+1                                                                              0.5                                                                              0.5                                                                              1  1+1                                           __________________________________________________________________________    Beta vulgaris                                                                            0  0  0  0  0  0  0  0                                             Avena fatua                                                                               97                                                                              100                                                                              100                                                                              100                                                                              98 100                                                                              100                                                                              100                                           Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                           Matricaria chamomilla                                                                     65                                                                              90 82 100                                                                              75 100                                                                              76 100                                           Active ingredient                                                                        III + XXXXII                                                                              III + XXXXIII                                          __________________________________________________________________________    Beta vulgaris                                                                            0  0  0  0  0  0  0  0                                             Avena fatua                                                                              75 100                                                                              85 100                                                                              76 97 85 100                                           Echinochloa crus-galli                                                                   100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                           Matricaria chamomilla                                                                    67 85 82 100                                                                              75 95 75 97                                            __________________________________________________________________________     0 = no damage                                                                 100 = complete destruction                                               

EXAMPLE 4

In the greenhouse, loamy sandy soil was filled into pots and sown withvarious seeds. The soil prepared in this manner was then treated withthe following amounts of the following individual active ingredients andcompositions thereof as emulsions or dispersions:

I 1-phenyl-4-amino-5-chloropyridazone-(6) 0.5, 1, 1.5, 1.86, 2.5, 3, 4and 5 kg/ha,

Iii o-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide, 0.5, 0.75,1, 1.25, 1.33, 1.5, 1.66, 2, 3, 4 and 5 kg/ha,

Iv 2,3-dichloroallyl N,N-diisopropylthiolcarbamate 0.25, 0.5, 0.75, 1,1.5, 2 and 4 kg/ha,

Xxiv o-(methylaminosulfonyl)-glycolic acid hexamethylene amide, 0.25,0.375, 0.5, 0.67, 0.725, 0.75, 0.834, 1, 1.5, 2, 2.5, 3, 3.5, 4 and 5kg/ha,

I+xxiv+iii 1+0.5+0.5, 1.5+0.75+0.75, 2+1+1, 2+0.5+1.5, 1.86+0.375+0.75,2.5+0.5+1, 3+0.725+1.25, 3+0.5+1.5, 2+0.67+1.33, 2.5+0.834+1.66 and2+1+2 kg/ha,

I+xxiv+iv 2+1+1, 2+1.5+0.5, 2+0.5+1.5, 1+0.5+0.5, 1+0.75+0.25, and1+0.25+0.75 kg/ha.

After 4 to 5 weeks it was ascertained that the compositions had a betterherbicidal action than their components, combined with superior cropplant compatibility.

The results are given below:

    __________________________________________________________________________    kg/ha       0.5                                                                              1                                                                              1.5                                                                             1.86                                                                             2 2.5                                                                             3  4  5                                              __________________________________________________________________________    Crop plants:                                                                  Beta vulgaris                                                                             0  0                                                                               0                                                                               0  0                                                                               0                                                                               0                                                                              10 15                                              Unwanted plants:                                                              Avena fatua 5 12                                                                              15                                                                              18 20                                                                              25                                                                              40                                                                              75 90                                              Echinochloa crus-galli                                                                    6 13                                                                              20                                                                              27 32                                                                              50                                                                              65                                                                              75 90                                              Stellaria media                                                                           20                                                                              45                                                                              60                                                                              70 80                                                                              90                                                                              95                                                                              100                                                                              100                                             Galium aparine                                                                            15                                                                              40                                                                              50                                                                              68 75                                                                              80                                                                              85                                                                              90 95                                              Chenopodium album                                                                         25                                                                              40                                                                              60                                                                              73 80                                                                              90                                                                              95                                                                              100                                                                              100                                             Alopecurus myosuroides                                                                    6 11                                                                              19                                                                              20 22                                                                              25                                                                              30                                                                              45 60                                              Lamium amplexicaule                                                                       10                                                                              20                                                                              25                                                                              33 40                                                                              60                                                                              70                                                                              90 100                                             Active ingredient                                                                            III                                                            kg/ha          0.5                                                                             0.75                                                                              1                                                                              1.25                                                                             1.33                                                                             1.5                                                                             1.66                                                                              2  3  4   5                                 __________________________________________________________________________    Beta vulgaris   0                                                                               0  0                                                                               0  0  0                                                                               0  0  0 10  20                                 Avena fatua    15                                                                              30 40                                                                              43 45 45                                                                              47 54 75 80  90                                 Echinochloa crus-galli                                                                       25                                                                              45 70                                                                              80 86 90                                                                              93 100                                                                              100                                                                              100 100                                Stellaria media                                                                              10                                                                              20 25                                                                              30 38 45                                                                              48 55 65 70  85                                 Galium aparine 10                                                                              12 15                                                                              18 22 25                                                                              26 30 40 43  45                                 Chenopodium album                                                                            15                                                                              17 20                                                                              25 30 35                                                                              38 45 50 57  65                                 Alopecurus myosuroides                                                                       20                                                                              40 50                                                                              60 75 90                                                                              94 100                                                                              100                                                                              100 100                                Lamium amplexicaule                                                                          10                                                                              15 20                                                                              25 27 35                                                                              40 55 60 70  75                                 Active ingredient                                                                          IV                                                               kg/ha        0.25                                                                             0.5                                                                              0.75                                                                              1                                                                              1.5                                                                               2                                                                              4                                                __________________________________________________________________________    Beta vulgaris                                                                              0  0  0   0                                                                              0  10                                                                              25                                               Avena fatua  10 20 30 50                                                                              83 95                                                                              100                                              Echinochloa crus-galli                                                                     0  10 15 20                                                                              40 50                                                                              90                                               Stellaria media                                                                            6  7  10 13                                                                              15 18                                                                              25                                               Galium aparine                                                                             0  0  0   0                                                                              5   8                                                                              15                                               Chenopodium album                                                                          0  5  7  10                                                                              15 20                                                                              33                                               Alopecurus myosuroides                                                                     11 26 35 58                                                                              85 95                                                                              100                                              Lamium amplexicaule                                                                        0  5  9  12                                                                              15 20                                                                              25                                               Active ingredient                                                                           XXIV                                                            kg/ha         0.25                                                                              0.375                                                                             0.5                                                                              0.67                                                                             0.725                                                                            0.75                                                                             0.834                                                                            1 1.5                                                                             2  2.5                               __________________________________________________________________________    Beta vulgaris  0   0   0  0  0  0  0  0                                                                               0                                                                               0  0                                Avena fatua   15  20  25 27 30 35 45 60                                                                              75                                                                              80 85                                Echinochloa crus-galli                                                                      20  31  35 39 42 45 55 60                                                                              90                                                                              100                                                                              100                               Stellaria media                                                                             20  23  25 27 28 30 40 50                                                                              75                                                                              85 90                                Galium aparaine                                                                             15  18  25 25 28 30 33 40                                                                              50                                                                              65 70                                Chenopodium album                                                                           15  20  30 31 33 35 37 40                                                                              45                                                                              60 65                                Alopecurus myosuroides                                                                      25  30  40 45 49 60 65 75                                                                              90                                                                              95 100                               Lamium amplexicaule                                                                         20  23  25 27 30 30 40 50                                                                              70                                                                              80 90                                Active ingredient                                                                           XXIV                                                            kg/ha         3    3.5  4    5                                                __________________________________________________________________________    Beta vulgaris 5    7    10   18                                               Avena fatua   90   96   100  100                                              Echinochloa crus-galli                                                                      100  100  100  100                                              Stellaria media                                                                             95   100  100  100                                              Galium aparine                                                                              75   80   85   95                                               Chenopodium album                                                                           70   80   90   100                                              Alopecurus myosuroides                                                                      100  100  100  100                                              Lamium amplexicaule                                                                         95   100  100  100                                              Active ingredient                                                                          I + XXIV + III                                                                1+  1.5+ 2+  2+  1.86+                                                                              2.5+                                                                              3+   3+                                             0.5+                                                                              0.75+                                                                              1+  0.5+                                                                              0.375                                                                              0.5+                                                                              0.725+                                                                             0.5+                              kg/ha        0.5 0.75 1   1.5 +0.75                                                                              1   1.25 1.5                               __________________________________________________________________________    Beta vulgaris                                                                               0   0    0   0   0    0   0    0                                Avena fatua   92 100  100 100 100  100 100  100                               Echinochloa crus-galli                                                                     100 100  100 100 100  100 100  100                               Stellaria media                                                                            100 100  100 100 100  100 100  100                               Galium aparine                                                                             100 100  100 100 100  100 100  100                               Chenopodium album                                                                          100 100  100 100 100  100 100  100                               Lamium amplexicaule                                                                         95 100  100 100 100  100 100  100                                             I + XXIV + III                                                                           I + XXIV + IV                                                      2+  2.5+        2+ 2+ 1+ 1+  1+                                               0.67+                                                                             0.834+                                                                            2+1     1.5+                                                                             0.5+                                                                             0.5+                                                                             0.73+                                                                             0.25+                                            1.33                                                                              1.66                                                                              +2 2+1+1                                                                              0.5                                                                              1.5                                                                              0.5                                                                              0.25                                                                              0.75                               __________________________________________________________________________    Beta vulgaris  0   0   0  0    0  0  0  0   0                                 Avena fatua   100 100 100                                                                              100  100                                                                              100                                                                               97                                                                              100 100                                Echinochloa crus-galli                                                                      100 100 100                                                                              100  100                                                                              100                                                                              100                                                                              100 100                                Stellaria media                                                                             100 100 100                                                                              100  100                                                                              100                                                                              100                                                                              100 100                                Galium aparine                                                                              100 100 100                                                                              100  100                                                                              100                                                                              100                                                                              100  95                                Chenopodium album                                                                           100 100 100                                                                              100  100                                                                              100                                                                              100                                                                              100  90                                Alopecurus myosuroides                                                                      100 100 100                                                                              100  100                                                                              100                                                                              100                                                                              100 100                                Lamium amplexicaule                                                                         100 100 100                                                                              100  100                                                                              100                                                                               95                                                                               90  75                                __________________________________________________________________________

EXAMPLE 5

In the greenhouse, loamy sandy soil was filled into pots and sown withvarious seeds. The soil prepared in this manner was then treated withthe following amounts of the following individual active ingredients andcompositions thereof as dispersions or emulsions:

I 1-phenyl-4-amino-5-chloropyridazone-(6) 0.5, 1, 1.5, 2, 2.5, 3, 4, 5and 6 kg/ha,

Iii o-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide 0.25, 0.5,0.75, 1, 1.5, 2, 2.5, 3, 4, 5 and 6 kg/ha,

Iv 2,3-dichloroallyl N,N-diisopropylthiolcarbamate 0.25, 0.5, 0.75, 1,1.5, 2 and 4 kg/ha,

Xxxxvi2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methyl-N-acetylaminosulfonate0.25, 0.5, 0.75, 1, 1.5, 2, 3, 4 and 6 kg/ha,

I+iii+iv 2+1+1, 2+1.5+0.5, 2+0.5+1.5, 1+0.5+0.5, 1+0.75+0.25, and1+0.25+0.75 kg/ha,

I+iii+xxxxvi 1.5+0.75+0.75, 2+1+1, 0.5+0.25+0.25, 1+0.5+0.5, 2+1.5+0.5,2+0.5+1.5, 3+1.5+1.5, 3+1+2 and 3+2+1 kg/ha.

After 4 to 5 weeks it was ascertained that the compositions had a betterherbicidal action than their components, combined with superior cropplant compatibility.

The results are given below:

    __________________________________________________________________________    Active ingredient                                                                          I                                                                kg/ha        0.5                                                                               1                                                                              1.5                                                                               2                                                                              2.5                                                                               3                                                                              4   5    6                                        __________________________________________________________________________    Crop plants:                                                                  Beta vulgaris                                                                              0   0                                                                              0   0                                                                              0   0                                                                              10  15   20                                       Unwanted plants:                                                              Avena fatua  5  12                                                                              15 20                                                                              25 40                                                                              75  90  100                                       Echinochloa crus-galli                                                                     6  13                                                                              20 32                                                                              50 65                                                                              75  90  100                                       Stellaria media                                                                            20 45                                                                              60 80                                                                              90 95                                                                              100 100 100                                       Galium aparine                                                                             15 40                                                                              50 75                                                                              80 85                                                                              90  95  100                                       Chenopodium album                                                                          25 40                                                                              60 80                                                                              90 95                                                                              100 100 100                                       Alopecurus myosuroides                                                                     6  11                                                                              19 22                                                                              25 30                                                                              45  60   95                                       Lamium amplexicaule                                                                        10 20                                                                              25 40                                                                              60 70                                                                              90  100 100                                       Active ingredient                                                                          III                                                              kg/ha        0.25                                                                              0.5                                                                             0.75                                                                              1                                                                              1.5                                                                              2 2.5                                                                              3   4   5   6                                 __________________________________________________________________________    Beta vulgaris                                                                              0   0 0   0                                                                               0                                                                              0   0 0   10  20  30                                Avena fatua  10  15                                                                              30 40                                                                              45                                                                              54 70 75  80  90  85                                Echinochloa crus-galli                                                                     20  25                                                                              45 70                                                                              90                                                                              100                                                                              100                                                                              100 100 100 100                               Stellaria media                                                                            5   10                                                                              20 25                                                                              45                                                                              55 60 65  70  85  100                               Galium aparine                                                                             5   10                                                                              12 15                                                                              25                                                                              30 35 40  43  45  60                                Chenopodium album                                                                          10  15                                                                              17 20                                                                              35                                                                              45 60 50  57  65  75                                Alopocurus myosuroides                                                                     10  20                                                                              40 50                                                                              90                                                                              100                                                                              100                                                                              100 100 100 100                               Lamium amplexicaule                                                                        7   10                                                                              15 20                                                                              35                                                                              55 70 60  70  75  90                                Active ingredient                                                                          IV                                                               kg/ha        0.25                                                                             0.5                                                                              0.75                                                                             1 1.5                                                                               2                                                                               4                                               __________________________________________________________________________    Beta vulgaris                                                                              0  0  0  0 0  10                                                                              25                                               Avena fatua  10 20 30 50                                                                              85 95                                                                              100                                              Echinochloa crus-galli                                                                     0  10 15 20                                                                              40 50                                                                              90                                               Stellaria media                                                                            6  7  10 13                                                                              15 18                                                                              25                                               Galium aparine                                                                             0  0  0  0 5   8                                                                              15                                               Chenopodium album                                                                          0  5  7  10                                                                              15 20                                                                              35                                               Alopecurus myosuroides                                                                     11 26 35 58                                                                              85 95                                                                              100                                              Lamium amplexicaule                                                                        0  5  9  12                                                                              15 20                                                                              25                                               Active ingredient                                                                          VIII                                                             kg/ha        0.25                                                                             0.5                                                                              0.75                                                                             1 1.5  2  3  4                                          __________________________________________________________________________    Beta vulgaris                                                                              0  0  0  0 0    0  5  10                                         Avena fatua  30 45 65 80                                                                              100 100                                                                              100                                                                              100                                         Echinochloa crus-galli                                                                     50 70 80 90                                                                              100 100                                                                              100                                                                              100                                         Stellaria media                                                                            50 60 65 75                                                                              95  100                                                                              100                                                                              100                                         Galium aparine                                                                             10 20 30 40                                                                              52   70                                                                               80                                                                               95                                         Chenopodium album                                                                          20 30 37 45                                                                              65   75                                                                               85                                                                               95                                         Alopecurus myosuroides                                                                     35 50 65 75                                                                              96  100                                                                              100                                                                              100                                         Lamium amplexicaule                                                                        15 25 50 70                                                                              80   90                                                                              100                                                                              100                                         Active ingredient                                                                          I + III + IV                                                                     2+ 2+ 1+ 1+  1+                                                            2+1                                                                              1.5+                                                                             0.5+                                                                             0.5+                                                                             0.75+                                                                             0.25+                                            kg/ha        +1 0.5                                                                              1.5                                                                              0.5                                                                              0.25                                                                              0.75                                             __________________________________________________________________________    Crop plants:                                                                  Beta vulgaris                                                                               0  0  0  0  0   0                                               Unwanted plants:                                                              Avena fatua  100                                                                              100                                                                              100                                                                               90                                                                               85  95                                              Echinochloa crus-galli                                                                     100                                                                              100                                                                              100                                                                               90                                                                              100  90                                              Stellaria media                                                                            100                                                                              100                                                                              100                                                                              100                                                                              100 100                                              Galium aparine                                                                             100                                                                              100                                                                              100                                                                               90                                                                               95  85                                              Chenopodium album                                                                          100                                                                              100                                                                              100                                                                               85                                                                               85  83                                              Alopecurus myosuroides                                                                     100                                                                              100                                                                              100                                                                              100                                                                              100 100                                              Lamium amplexicaule                                                                        100                                                                              100                                                                              100                                                                               75                                                                               75  78                                              Active ingredient                                                                          I + III + XXXVI                                                               1.5+     0.5+                                                                              1+ 2+ 2+ 3+                                                      0.75+    0.25+                                                                             0.5+                                                                             1.5+                                                                             0.5+                                                                             1.5+                                       kg/ha        0.75                                                                              2+1+1                                                                              0.25                                                                              0.5                                                                              0.5                                                                              1.5                                                                              1.5                                                                              3+1+2                                                                              3+2+1                              __________________________________________________________________________    Beta vulgaris                                                                               0   0    0   0  0  0  0  0    0                                 Avena fatua  100 100  75   97                                                                              100                                                                              100                                                                              100                                                                              100  100                                Echinochloa crus -galli                                                                    100 100  86  100                                                                              100                                                                              100                                                                              100                                                                              100  100                                Stellaria media                                                                            100 100  80  100                                                                              100                                                                              100                                                                              100                                                                              100  100                                Galium aparine                                                                             100 100  75  100                                                                              100                                                                              100                                                                              100                                                                              100  100                                Chenopodium album                                                                          100 100  65   90                                                                              100                                                                              100                                                                              100                                                                              100  100                                Alopecurus myosuroides                                                                     100 100  75  100                                                                              100                                                                              100                                                                              100                                                                              100  100                                Lamium amplexicaule                                                                        100 100  75  100                                                                              100                                                                              100                                                                              100                                                                              100  100                                __________________________________________________________________________     0 = no damage                                                                 100 + complete destruction                                               

I claim:
 1. A herbicide composition comprising an inert carrier havingdispersed therein a herbicidally effective amount of a mixtureconsisting essentially of 20-80 wt % of each of:a.O-(methylaminosulfonyl)-glycolic acid-N-isopropylanilideO-(isopropylaminosulfonyl)-glycolic acid N-butyn-1-yl-3-anilide, orO-(methylaminosulfonyl)-glycolic acid hexamethylene amide, b.1-phenyl-4-amino-5-chloropyridazone-(6), and c. 2,3-dichloroallylN,N-diisopropylthiolcarbamate 2,3,3-trichloroallylN,N-diisopropylthiolcarbamate ethyl N-ethyl-N-cyclohexylthiolcarbamate,ethyl N,N-di-n-propylthiolcarbamate or n-propylN-ethyl-N-n-butylthiolcarbamate.
 2. A herbicide composition as claimedin claim 1, wherein compound (a) is O-(methylaminosulfonyl)-glycolicacid-N-isopropylanilide and compound (c) is 2,3-dichloroallylN,N-diisopropylthiolcarbamate, 2,3,3-trichloroallylN,N-diisopropylthiolcarbamate, or ethylN-ethyl-N-cyclohexylthiolcarbamate.
 3. A herbicide composition asclaimed in claim 1, wherein compound (a) isO-(isopropylaminosulfonyl)-glycolic acid-N-butyn-1-yl-3-anilide orO-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide, and compound(c) is ethyl N,N-di-n-propylthiolcarbamate or n-propylN-ethyl-N-n-butylthiolcarbamate.
 4. A herbicide composition as claimedin claim 1, wherein compound (a) is O-(methylaminosulfonyl)-glycolicacid hexamethylene amide, and compound (c) is 2,3-dichloroallylN,N-diisopropylthiolcarbamate.
 5. A herbicide composition as claimed inclaim 1, wherein compound (a) is O-(methylaminosulfonyl)-glycolicacid-N-isopropylanilide, and compound (c) is 2,3-dichloroallylN,N-diisopropylthiolcarbamate.